Chiral beta-keto acid undergoes base-catalyzed decarboxylation

Steps:

• Check chirality: requires a stereogenic carbon with four different groups.
• Identify CO2-releasing reaction: beta-keto acids or malonic derivatives decarboxylate with NaOH via beta-elimination after deprotonation.
• Examine options: test each for a chiral center and beta-keto/malonic functionality.
• Confirm D meets both criteria while others fail one or both.

Why D is correct:

• D is 2-methyl-3-oxobutanoic acid, with chiral C2 (groups: H, CH3, COOH, COCH3) and beta-keto setup enabling decarboxylation per the mechanism: enol formation, then CO2 loss to ketone.

Why the others are wrong:

• A: Acetic acid derivative; achiral, no beta-carbonyl for decarboxylation.
• B: Simple chiral alcohol; lacks acidic beta-group, forms salt but no CO2.
• C: Symmetric dicarboxylic acid; achiral, decarboxylates but no stereocenter.

Final answer: D